1-methyl-4-oxocyclohex-2-enecarbonitrile | 133828-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-4-oxocyclohex-2-enecarbonitrile
• 英文别名: 1-Methyl-4-oxocyclohex-2-ene-1-carbonitrile
• CAS: 133828-05-4
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: FUOWQLQSDJGOAD-UHFFFAOYSA-N

物化性质

• 沸点：
  279.2±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-oxocyclohex-2-enecarbonitrile 在 lithium aluminium tetrahydride 作用下， 以93%的产率得到4-Aminomethyl-4-methyl-cyclohex-2-enol
  参考文献：
  名称：

  Transition metal mediated asymetric synthesis

  摘要：

  Tricarbonyl(eta-5-2-methoxy-5-methylcyclohexadienyl)iron(1 +) hexafluorophosphate(1 -) has been converted into a dehydroisoquinuclidine. Although the scope of the process is limited by competing aromatisation during removal of the tricarbonyliron group from the organic ligand, it is appropriate in situations where substituents block aromatisation. Cyclisation to the dehydroisoquinuclidine is facilitated by the use of an intermediate bearing a secondary amine.

  DOI：

  10.1016/0022-328x(91)86260-w
• 作为产物：
  描述：

  2-methoxy-1-methyl-4-((trimethylsilyl)oxy)cyclohex-3-enecarbonitrile 在 盐酸 、 四氯化钛 作用下， 生成 1-methyl-4-oxocyclohex-2-enecarbonitrile
  参考文献：
  名称：

  Acid catalyzed rearrangements of 4-methyl-4-cyanocyclohexadienone

  摘要：

  Acid-catalyzed dienone-phenol rearrangement reactions of 4-methyl-4-cyanocyclohexadienone occur very slowly and give either fragmentation or methyl group migration, not cyano group migration, under non-nucleophilic strongly acidic conditions.

  DOI：

  10.1016/0040-4039(91)85002-m

文献信息

• [EN] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS<br/>[FR] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES EN TANT QU'INHIBITEURS DE JANUS KINASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013040863A1

  公开（公告）日：2013-03-28

  Cycloalkylnitrile pyrazole carboxamides as JAK inhibitors useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer are provided.

  提供环烷基腈吡唑羧酰胺作为JAK抑制剂，用于治疗JAK介导的疾病，如类风湿关节炎、哮喘、慢性阻塞性肺病和癌症。
• MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF
  申请人：Honda Tadashi

  公开号：US20110196007A1

  公开（公告）日：2011-08-11

  The present invention features monocyclic cyanoenone compositions and methods for using the same in the treatment of diseases such as cancer, inflammatory diseases and neurodegenerative diseases.

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。
• CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20140243309A1

  公开（公告）日：2014-08-28

  The instant invention provides compounds of formula I which are JAK inhibitors, and as such are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

  本发明提供了I式化合物，它们是JAK抑制剂，因此可用于治疗JAK介导的疾病，如类风湿性关节炎、哮喘、慢性阻塞性肺疾病和癌症。
• Synthesis, Chemical Reactivity as Michael Acceptors, and Biological Potency of Monocyclic Cyanoenones, Novel and Highly Potent Anti-inflammatory and Cytoprotective Agents
  作者：Suqing Zheng、Y. R. Santosh Laxmi、Emilie David、Albena T. Dinkova-Kostova、Katherine H. Shiavoni、Yanqing Ren、Ying Zheng、Isaac Trevino、Ronald Bumeister、Iwao Ojima、W. Christian Wigley、James B. Bliska、Dale F. Mierke、Tadashi Honda

  DOI：10.1021/jm3003922

  日期：2012.5.24

  Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g., CDDO and bardoxolone methyl) and tricycles (e.g., TBE-31). Among monocyclic cyanoenones, 1 is a highly reactive Michael acceptor with thiol nucleophiles. Furthermore, an important feature of 1 is that its Michael addition is reversible. For the inhibition of NO production, 1 shows the highest potency. Notably, its potency is about three times higher than CDDO, whose methyl ester (bardoxolone methyl) is presently in phase III clinical trials. For the induction of NQO1, 1 also demonstrated the highest potency. These results suggest that the reactivity of these Michael acceptors is closely related to their biological potency. Interestingly, in LPS-stimulated macrophages, 1 causes apoptosis and inhibits secretion of TNF-alpha and IL-1 beta with potencies that are higher than those of bardoxolone methyl and TBE-31.
• Inokuchi; Okano; Miyamoto, Synlett, 2000, # 11, p. 1549 - 1552
  作者：Inokuchi、Okano、Miyamoto、Bte Madon、Takagi

  DOI：——

  日期：——